Design, synthesis, and biological testing of pyrazoline derivatives of combretastatin-A4

Bioorganic and Medicinal Chemistry Letters

Volumn 17, Issue 21, 2007, Pages 5897-5901

  Johnson, Marlie ^a   Younglove, Brent ^a   Lee, Lauren ^a   LeBlanc, Regan ^b   Holt Jr , Herman ^c   Hills, Patrice ^d   Mackay, Hilary ^b   Brown, Toni ^b   Mooberry, Susan L ^d   Lee, Moses ^a,b  

^a HOPE COLLEGE   (United States)

^b FURMAN UNIVERSITY   (United States)

^c UNIVERSITY OF NORTH CAROLINA AT ASHEVILLE   (United States)

^d SOUTHWEST FOUNDATION FOR BIOMEDICAL RESEARCH   (United States)

Author keywords

Achiral; Anti cancer; CC 1065; Combretastatins; Dimer; Duocarmycins; Pyrazolines; Pyrrolobenzodiazepines; seco Amino CBI; Tubulin

Indexed keywords

2,5 DIMETHOXYPYRAZOLINE DERIVATIVE; 3,4,5 TRIMETHOXYPYRAZOLINE DERIVATIVE; ACETIC ACID DERIVATIVE; COMBRETASTATIN A4; PYRAZOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTINEOPLASTIC ACTIVITY; ARTICLE; CYTOTOXICITY; DRUG ACETYLATION; DRUG ACTIVITY; DRUG DESIGN; DRUG SYNTHESIS; IC 50; MICROTUBULE ASSEMBLY; MOUSE; NONHUMAN; POLYMERIZATION;

ANIMALS; CELL LINE; DRUG DESIGN; MICE; MODELS, MOLECULAR; PYRAZOLES; STILBENES;

EID: 34548838284     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2007.07.105     Document Type: Article

References (31)

1. Pettit G.R., Bux S., Singh B., Niven M.L., Hamel E., and Schimdt J.M. J. Nat. Prod. 50 (1987) 119
2. Chen S., Tan U., Chang C., Chen T., Lin C., Chang Y., and Wang C. Bioorg. Med. Chem. Lett. 12 (2002) 101
3. Pettit G.R., Singh S.B., Boyd M.R., Hamel E., Pettit R.K., Schimdt J.M., and Hogan F. J. Med. Chem. 38 (1995) 1666
4. Gaukoger K., Hadfield J.A., Hepworth L.A., Lawrence N.J., and McGown A.T. J. Org. Chem. 66 (2001) 8135
5. Lawrence N.J., Rennison D., McGown A.T., Ducki S., Gul L.A., Hadfield J.A., and Khan N. J. Comb. Chem. 3 (2001) 421
6. McGown A.T., and Fox B.W. Anti-Cancer Drug Des. 3 (1989) 249
7. Vincent L., Kermani P., Young L.M., Cheng J., Zhang F., Shido K., Lam G., Bompais-Vincent H., Zhu Z., Hicklin D.J., Bohlen P., Chaplin D.J., May C., and Rafii S. J. Clin. Invest. 115 (2005) 2992
8. Galbraith S.M., Maxwel R.J., Lodge M.A., Tozer G.M., Wilson J., Taylor N.J., Stirling J.J., Sena L., Padhani A.R., and Rustin G.S. J. Clin. Oncol. 15 (2003) 2831
9. Hinnen P., and Eskens F.A. Br. J. Cancer 96 (2007) 1159
10. Getahun Z., Jurd L., Ping S.C., Chii M.L., and Hamel E. J. Med. Chem. 35 (1992) 1058
11. Dimmock J.R., Kandepu N.M., Hetherington M., Quail J.W., Pugazhenthi U., Sudom A.M., Chamankhah M., Rose P., Pass E., Allen T.M., Halleran S., Szydlowski J., Mutus B., Tannous M., Manavathu E.K., Myers T.G., De Clercq E., and Balzarini J. J. Med. Chem. 41 (1998) 1014
12. Kim Y., Nam N.-H., You Y.-J., and Ahn B.-Z. Bioorg. Med. Chem. Lett. 12 (2002) 719
13. Ohsumi K., Hatanaka T., Fujita K., Nakagawa R., Fukuda Y., Nihei Y., Suga Y., Morinaga y., Akiyama Y., and Tsuji T. Bioorg. Med. Chem. Lett. 8 (1998) 3153
14. Kaffy J., Monneret C., Mailliet P., Commerçon A., and Pontinkis R. Tetrahedron Lett. 45 (2004) 3359
15. Wang L., Woods K.W., Li Q., Barr K.J., McCroskey R.W., Hannick S.M., Gherke L., Credo R.B., Hui Y.-H., Marsh K., Warner R.J., Lee Y., Zielinski-Mozng N., Frost D., Rosenberg S.-H., and Sham H.L. J. Med. Chem. 45 (2002) 1697
16. Sun L., Vasilevich N.I., Fuselier J.A., Hocart S.J., and Coy D.H. Bioorg. Med. Chem. Lett. 14 (2004) 2041
17. LeBlanc R., Dickson J., Brown T., Stewart M., Pati H., VanDerveer D., Arman H., Harris J., Pennington W., Holt H., and Lee M. Bioorg. Med. Chem. 13 (2005) 6025
18. Ducki S., Forrest R., Hadfield J.H., Kendall A., Lawrence N.J., McGown A.T., and Rennison D. Bioorg. Med. Chem. Lett. 8 (1998) 1051
19. Ruprich J., Prout A., Dickson J., Younglove B., Nolan L., Baxi K., LeBlanc R., Forrest L., Hills P., Holt H., Mackay H., Brown T., Mooberry S., and Lee M. Lett. Drug Des. Disc. 4 (2007) 144
20. Cox C., Breslin M., Mariano B., Coleman P., Buser C., Walsh E., Hamilton K., Huber H., Kohl N., Torrent M., Yan Y., Kuo L., and Hartman G. Bioorg. Med. Chem. Lett. 15 (2005) 2041
21. Fraley M., Garbaccio R.M., Arrington K.L., Hoffman W.F., Tasber E.S., Coleman P.J., Buser C.A., Walsh E.S., Hamilton K., Fernandes C., Schaber M.D., Lobell R.B., Tao W., South V.J., Yan Y., Kuo L., Prueksaritanont T., Shu C., Torrent M., Heimbrook D.C., Kohl N.E., Huber H.E., and Hartman G.D. Bioorg. Med. Chem. Lett. 16 (2006) 1775
22. Garbaccio R.M., Fraley M.E., Tasber E.S., Olson C.M., Hoffman W.F., Arrington K.L., Torrent M., Buser C.A., Walsh E.S., Hamilton K., Schaber M.D., Fernandes C., Lobell R.B., Tao W., South V.J., Yan Y., Kuo L.C., Prueksaritanont T., Slaughter D.E., Shu C., Heimbrook D.C., Kohl N.E., Huber H.E., and Hartman G.D. Bioorg. Med. Chem. Lett. 16 (2006) 1780
23. Dickson J., Flores L., Stewart M., Holt Jr. H.L., LeBlanc R., and Lee M. J. Chem. Ed. 83 (2006) 934
24. Pati H.N., Holt Jr. H.L., LeBlanc R., Dickson J., Stewart M., Brown T., and Lee M. Med. Chem. Res. 14 (2005) 19
25. 5 358.1529 found 358.1527.
26. Lévai A. ARKIVOC ix (2005) 344
27. 6 400.1634, found 400.1634.
28. Dorr R.T., Dvorakova K., Snead K., Alberts D.S., Salmon S.E., and Pettit G.R. Invest. New Drugs 14 (1996) 131
29. Pettit G.R., Singh S.B., Hamel E., Lin C.M., Alberts D.S., and Garcia-Kendall D. Experientia 45 (1989) 209
30. Kong Y., Grembecka J., Edler M.C., Hamel E., Mooberry S.L., Sabat M., Rieger J., and Brown M.L. Chem. Biol. 12 (2005) 1007
31. Ravelli R.B.G., Gigant B., Curmi P.A., Jourdain I., Lachkar S., Sobel A., and Knossow M. Nature 428 (2004) 198